Preparation and X-Ray Crystal Structure of 3-(4-(Dimethylamino)phenyl)-2-(phenylamino)isoquinolin-1(2H)-one, 3-(4-Methoxyphenyl)-2-(phenylamino)isoquinolin-1(2H)-one, and 2-Methyl-N-/i>-(4-methylbenzoyl)-N-/i>-phenylbenzohydrazide

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• 作者：William G. Shuler (1) r>Ellyn A. Smith (1) r>Sloan M. Hess (1) r>Thomas M. C. McFadden (1) r>Clyde R. Metz (1) r>Donald G. VanDerveer (2) r>William T. Pennington (2) r>Phillip J. Mabe (1) r>Shabree L. Knick (1) r>Charles F. Beam (1) beamc@cofc.edu
• 关键词：Multiple anion synthesis – Isoquinolinones – N ; acylated hydrazide
• 刊名：Journal of Chemical Crystallography
• 出版年：2012
• 出版时间：September 2012
• 年：2012
• 卷：42
• 期：9
• 页码：952-959
• 全文大小：501.5 KB
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• 作者单位：1. Department of Chemistry and Biochemistry, College of Charleston, Charleston, SC 29424, USA2. Department of Chemistry, Clemson University, Clemson, SC 29634, USA
• ISSN：1572-8854

文摘

Abstract 2-Methylbenzoic acid phenylhydrazide was polylithiated with excess lithium diisopropylamide, and the resulting polylithiated intermediate was condensed with methyl 4-dimethylaminobenzoate or methyl 4-methoxybenzoate to afford C-acylated intermediates that were immediately acid cyclized to afford 3-(4-(dimethylamino)-phenyl)-2-(phenylamino)isoquinolin-1(2H)-one C₂₃H₂₁N₃O or 3-(4-methoxyphenyl)-2-(phenylamino)isoquinolin-1(2H)-one C₂₂H₁₈N₂O₂. The polylithiated intermediate underwent N-acylation when it was condensed with methyl 4-methylbenzoate to give 2-methyl-N′-(4-methylbenzoyl)-N′-phenylbenzohydrazide C₂₂H₂₀N₂O₂. Crystals of C₂₃H₂₁N₃O 4a are triclinic, P [`1] \overline{1} , a = 9.138(2) ?, b = 10.519(2) ?, c = 11.082(2) ?, α = 91.55(3)°, β = 108.92(3)°, γ = 111.16(3)°, Z = 2, V = 927.1(3) ?3, R ₁ = 0.0711 and wR ₂ = 0.1828 for reflections with I > 2σ(I); crystals of C₂₂H₁₈N₂O₂ 4b are monoclinic, P2₁/c, a = 8.821(1) ?, b = 13.276(2) ?, c = 15.482(3) ?, β = 105.271(4)°, Z = 4, V = 1748.9(5) ?3, R ₁ = 0.0416 and wR ₂ = 0.1030 for reflections with I > 2σ(I); crystals of C₂₂H₂₀N₂O₂ 3 are orthorhombic, Pbca, a = 13.505(3) ?, b = 9.733(2) ?, c = 28.601(6) ?, Z = 8, V = 3759.4(13) ?3, R ₁ = 0.1683 and wR ₂ = 0.3526 for reflections with I > 2σ(I).